STEREOCHEMISTRY OF THE BAKERS-YEAST MEDIATED REDUCTION OF THE C=C BOND OF (Z)-5-BENZOYLOXYHEX-3-EN-2-ONE AND (E)-5-BENZOYLOXYHEX-3-EN-2-ONE

被引：18

作者：

FRONZA, G

FUGANTI, C

GRASSELLI, P

LANATI, S

RALLO, R

TCHILIBON, S

机构：

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 20期

关键词：

D O I：

10.1039/p19940002927

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Baker's yeast reduction of the Z and E enones 5 and 6 to the methyl ketone 7 proceeds with kinetic preference for the R and S enantiomers, respectively. However irrespective of the double-bond stereochemistry end of the absolute configuration of the oxygen-bearing carbon atom at position 5. the C=C bond reduction occurs by formal anti addition of hydrogen, with delivery of the hydrogen atom at position 4 from the re-face of the molecule, as shown by H-2 NMR studies onto lactones 17 and 18 obtained in experiments with deuteriated precursors.

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页码：2927 / 2930

页数：4

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